Diastereoselective Fischer-type pyrroloindole synthesis and its application to the synthesis of chiral pyrroloindole alkaloids

被引：18

作者：

Nishida, A ^{[1
]}

Ushigome, S ^{[1
]}

Sugimoto, A ^{[1
]}

Arai, S ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

HETEROCYCLES | 2005年 / 66卷

关键词：

asymmetric synthesis; esermethole; Fischer indole synthesis; physostigmine; pyrroloindole;

D O I：

10.3987/COM-05-S(K)71

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.

引用

页码：181 / 185

页数：5

共 50 条

[41] Totally diastereoselective synthesis of a new chiral quinoline diazaphospholidine ligand and its derivatives
Delapierre, G
Achard, M
Buono, G
TETRAHEDRON LETTERS, 2002, 43 (22) : 4025 - 4028
[42] SYNTHESIS, STRUCTURE, AND DYNAMIC PROPERTIES OF A FULVALENE-BOUND FISCHER-TYPE CARBENE COMPLEX - A NOVEL THERMAL ELIMINATION OF PROPENE
DRAGE, JS
VOLLHARDT, KPC
ORGANOMETALLICS, 1985, 4 (01) : 191 - 192
[43] A CHIRAL SYNTHESIS OF (-)-CANNABISATIVINE - AN APPLICATION OF THE HIGHLY DIASTEREOSELECTIVE HETERO-DIELS-ALDER REACTION
HAMADA, T
ZENKOH, T
SATO, H
YONEMITSU, O
TETRAHEDRON LETTERS, 1991, 32 (13) : 1649 - 1652
[44] Enantiodivergent synthesis of a decalin type of Chiral building blocks and their application to terpenoid synthesis
Toyooka, N
Nishino, A
Momose, T
TETRAHEDRON, 1997, 53 (18) : 6313 - 6326
[45] Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines
Nenajdenko, Valentine G.
Reznichenko, Alexander L.
Balenkova, Elizabeth S.
TETRAHEDRON, 2007, 63 (14) : 3031 - 3041
[46] Synthesis of chiral polymers and its application in asymmetric reduction
Cha, Rui-Tao
Li, Quan-an Li
Chen, Na-Li
Wang, Yun-Pu
JOURNAL OF APPLIED POLYMER SCIENCE, 2007, 103 (01) : 148 - 152
[47] Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar
Fan, Shilu
He, Chun-Yang
Zhang, Xingang
TETRAHEDRON, 2010, 66 (27-28) : 5218 - 5228
[48] A NEW EFFICIENT AMINOLYSIS AND ITS APPLICATION TO SYNTHESIS OF MACROLACTAM ALKALOIDS
FUJITA, E
PURE AND APPLIED CHEMISTRY, 1981, 53 (06) : 1141 - 1154
[49] CHIRAL SYNTHESIS OF D-HOMOSERINE AND ITS APPLICATION TO SYNTHESIS OF NOCARDICIN-A
COOPER, RDG
JOSE, F
MCSHANE, L
KOPPEL, GA
TETRAHEDRON LETTERS, 1978, (26) : 2243 - 2246
[50] Synthesis of the first stable Fischer-type carbene metal complex with a C-O-P structural motive of the carbene ligand
Streubel, R
Hobbold, M
Priemer, S
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 613 (01) : 56 - 59

← 1 2 3 4 5 →